Enantioselective Synthesis of Ceralure B1, Ethyl cis-5-Iodo-trans-2-methylcyclohexane-1-carboxylate
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Add time:08/18/2019 Source:sciencedirect.com
Ethyl (1R, 2R, 5R)-5-iodo-2-methylcyclohexane-1-carboxylate is a potent attractant for the Mediterranean fruit fly. This compound was stereoselectively synthesized on a multigram scale in nine steps in 15% yield. Key steps of the synthesis involved an asymmetric Diels–Alder reaction, iodolactonization, stereoselective reduction of the carbonyl, and inversion of configuration with iodide.
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